Ethanol → HCID 14207582, compound

Participants

Reaction Steps

A solution of 4-ethyl-7-methyl-6-nitro-anthranil (300 mg, 0.000146 mol.) in absolute ethanol was mixed with sodium bicarbonate (160 mg, 0.0019 mol.) and was refluxed for 4 hrs. The solution was evaporated to dryness, the residue partitioned between ethyl acetate and 5% hydrochloric acid solution. The organic layer was dried over magnesium sulphate and evaporated to give a solid. This solid was further purified by column chromatography (10% ethyl acetate: pet. ether 30-60) to give ethyl 2-amino-6-ethyl-3-methyl-4-nitro-benzoate as an oil (yield: 276 mg, 76%). IR (neat): 3500, 3400, 2980, 1700, 1620, 1580, 1530 cm-1. H-NMR (CDCl3): 1.20 (t, 3H, CH3), 1.40 (t, 3H, CH3), 2.18 (s, 3H, CH3) 2.78 (q, 3H, CH2), 4.40 (q, 2H, CH2O), 5.05 (br.s, 2H, NH2), 6.91 (s, 1H, ArH).

Provenance & Evidence